Cl.[NH2:2][C:3]([NH2:5])=[NH2+:4].CC([O-])(C)C.[K+].C([O:14][C:15](=O)[CH2:16][CH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[CH:24]=2)[C:19](=[O:30])[N:18]1[CH2:31][C:32]([F:35])([F:34])[F:33])C.Cl>O>[O:30]=[C:19]1[C:20]2[C:25](=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=2)[CH:17]([CH2:16][C:15]([NH:4][C:3]([NH2:5])=[NH:2])=[O:14])[N:18]1[CH2:31][C:32]([F:34])([F:33])[F:35]
1.24 g guanidinium hydrochloride and 1.21 g of KOtBu were suspended using 30 ml of DMF(anhydrous) and stirred for 30 minutes at ambient temperature. Then, a solution of 0.8 g of [3-oxo-2-(2,2,2-trifluoro-ethyl)-6-trifluoromethyl-2,3-dihydro-1H-isoindol-1-yl]-acetic acid ethyl ester in 5 ml of DMF(anhydrous) were added and the mixture was stirred for 17 h at ambient temperature. The mixture was then poured into 100 ml of water and the pH was adjusted to pH=8 using aqueous HCl-solution. The aqueous layer was extracted three times using 100 ml of EA each. The organic layer was dried over MgSO4 and the solvent was removed in vacuo. Chromatography on silica gel using EA/MeOH 3:1 yielded 0.56 g of an amorphous solid (Rf(EA/MeOH 3:1)=0.45, MS (ES+): 383 (M+1)+).
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